Patent GB-543743-A (GB)
Title: Improvements in and relating to the dyeing and printing of fabrics and fibres made of cellulose esters and ethers
IPC: D06P3/34
Filed: 1940-07-06
Abstract: 543,743. Dyeing cellulose derivatives. COMPAGNIE RATIONALE DE MATIERES COLORANTES ET MANUFACTURES DE PRODUITS CHIMIQUES DU NORD REUNIES ETABLISSEMENTS KUHLMANN. July 6,1940, No. 11327. Convention date, July 8, 1939. [Classes 2 (iii) and 15 (ii)] Fibres and fabrics of cellulose esters or ethers are dyed or printed by applying thereto an aqueous dispersion of one of the following monoazo dyestuffs containing at least two alcoholic hydroxy groups contained in the group / R 1  -N  , wherein R 1  represents alkyl, hydroxy-    \ R 2  alkyl or dihydroxyalkyl and R  2  represents hydroxyalkyl, dihydroxyalkyl or hydroxycycloalkyl. The dyestuffs specified are (1) to (4) (yellow), 2- or 3-chloroaniline- N-di-(#- hydroxyethyl) - aniline or N - di - (#-hydroxyethyl) - 3 - toluidine, (5) to (9) (orange), 2:4:5 - trichloroaniline# N - di - (#-hydroxyethyl) - 3 - toluidine, N - di - (#-hydroxyethyl) - aniline, N - di - (#-hydroxyethyl) - 3<SP>1</SP> - chloroaniline, N - methyl - N - #:γ - dihydroxypropyl - aniline or N - ethyl - N - #:γ - dihydroxypropyl - aniline, (10) to (12) (brown) 2:6-dichloro-4-nitroaniline# N - di - (#-hydroxyethyl) - p - cresidine or N - di - (#-hydroxyethyl) - aniline, and monobrominated 4:5 - dinitro - 2 - aminoanisole# N - di - - (# - hydroxyethyl) - 3 chloroaniline, (13) to (15) (red), 5 - nitro - 2 - aminoanisole# N - - di - (# - hydroxyethyl) - aniline or N - di - (# - hydroxyethyl) - 3 - toluidine, and 2:5 - dichloro - 4 - nitroaniline# N - di - (# - hydroxyethyl) - 3 - chloroaniline, (16) to (18) (ruby), 2:5 - dichloro - 4 - nitroaniline# N - di - (# - hydroxyethyl) - aniline or N - ethyl - N - #: y - dihydroxypropyl - aniline, and 2:4- dinitroaniline# N - di - (# - hydroxyethyl) - 3 - chloroaniline, (19) to (21) (reddish violet), 2 : 5 - dichloro - 4 - nitroaniline# N - di - # - hydroxyethyl) - 3 - toluidine or N - di - (# - hydroxyethyl) - p - cresidine, and 2 4 - dinitroaniline# N - di - (# - hydroxyethyl) - aniline, (22) and (23) (violet), 4 - chloro - 2:6 - dinitro - 5 - aniinoanisole# N - di - (# - hydroxyethyl) - 3 - toluidine or N - di - (# - hydroxyethyl) - p - cresidine or N - ethyl - N - #:γ - dihydroxypropyl - p - cresidine, (24) and (25) (bluish violet), 4 - chloro - 2:6 - dinitro - 5 - aminoanisole# N - di - (# - hydroxyethyl) - p - cresidine or N - ethyl - N - #:γ - dihydroxypropyl - p - cresidine, (26) and (27) blue, 4 - chloro - 2:6 - dinitro-5 - aminoanisolethe 2 - N - 2<SP>1</SP>- hydroxycyclohexyl - N - # - hydroxyethylamino - and 2 - N - 2<SP>1</SP> - hydroxycyclohexyl - N - y - methoxy - # - hydroxypropylamino - derivatives of 4 - acetylaminoanisole. In an example, cellulose acetate rayon is dyed a fast ruby shade by treatment for half an hour with an aqueous liquor at 60‹ C. containing the dyestuff, 2:4 - dinitroaniline- N - di - (# - hydroxyethyl) - 3 - chloroaniline dispersed with the sodium salt of the condensation product of formaldehyde with naphthalene - 2 - sulphonic acid, followed by rinsing and drying, or a matt cellulose acetate rayon is printed with a preparation, thickened with gum senegal, containing the same dyestuff which has been ground with the sodium salt of isopropylnaphthalene - 2 - sulphonic acid, and the print is steamed. Specifications 274,823, 292,180; [both in Class 2 (iii)], 436,390, 450,099, 454,445, 460,276, 462,233 and 537,831 are referred to. N - di - (# - hydroxyethyl) p - cresidine is obtained by reaction of ethylene oxide (2 mols.) with p-cresidine (1 mol.) at 150‹ C. under pressure. N - ethyl - N - # : γ - dihydroxypropyl - p - cresidine is obtained by the action at 150‹ C. under pressure of ethyl chloride in alcohol and in presence of calcium carbonate on N-#-γ- dihydroxypropyl - p - cresidine obtained by heating p - cresidine (2 mols.) with glycerol -α - monochlorohydrin (1 mol.) in water for 18 hours under reflux.  The 2 - N - - 2<SP>1</SP> - - hydroxycyclohexyl N - # - hydroxyethyl amino- and 2 - N - - 2<SP>1</SP> - hydroxycyclohexyl N - γ -methoxy - # - hydroxypropylaminoderivatives of 4 - acetylaminoanisole are obtained by reaction respectively of ethylene oxide in chlorobenzene at 160‹ C. under pressure and of epichlorhydrin in methanol under reflux on the product of the action of cyclohexene oxide (1 mol.) on 2 - amino - 4 - acetyl aminoanisole (1 mol.) at 130-140‹ C. under pressure, the product in the latter case being boiled under reflux with a solution of potassium hydroxide in methanol to replace the chlorine by the methoxy group. 2 - Amino - 4 - acetylaminoanisole is obtained by reduction of 2-nitro-4-acetylaminoanisole. 4 - - Chloro - 2:6 - - dinitro 5 - aminoanisole is obtained by hydrolysis of the product of successive nitration and chlorination of 3- acetylaminoanisole. The Specification as open to inspection under Sect. 91 comprises also the use of a dispersion of any monoazo dyestuff containing two alcoholic hydroxy groups. This subject-matter does not appear in the Specification as accepted.